Methyl iodide → HCID 59769884, compound

Participants

Reaction Steps

Add 1.2 equiv of n-BuLi-hexanes dropwise to a solution of 4-methylene-9,10-dihydro-4H-3-thia-1-aza-benzo[f]azulene (prepared from 9,10-dihydro-3-thia-1-aza-benzo[f]azulen-4-one (see Scheme XIII(b) as in Preparation 23) in THF (0.08 M) at −78° C. under Ar. Stir the resultant dark green solution for 5 min before adding 1.2 equiv of iodomethane in THF. Allow to warm and stir at room temperature for 18 h before quenching with excess water. Separate layers and extract the aqueous layer with diethyl ether (3×) and then dry (MgSO4) and concentrate the combined organic layers under reduced pressure. Use in the next step without further purification: 1H NMR (CDCl3, 400 MHz) δ 2.60 (s, 3 H), 3.03-3.13 (m, 4 H), 5.34 (s, 1 H), 5.53 (s, 1 H), 7.20-7.28 (m, 3 H), 7.33 (m, J=7.2 Hz, 1 H). TLC Rf=0.30 (10% EtOAc:hexanes).

Provenance & Evidence